CAS 2686-70-6

(2S)-2-Amino-4-sulfinobutanoic acid

Description:

(2S)-2-Amino-4-sulfinobutanoic acid, commonly known as methionine sulfoxide, is an amino acid derivative characterized by the presence of a sulfoxide functional group. It is a chiral compound, with the (2S) configuration indicating the specific spatial arrangement of its atoms. This substance plays a significant role in biological systems, particularly in the context of protein synthesis and oxidative stress, as it can be formed from the oxidation of methionine residues in proteins. Methionine sulfoxide is soluble in water and exhibits properties typical of amino acids, such as the ability to participate in hydrogen bonding and form zwitterionic structures. Its sulfinyl group contributes to its reactivity and potential interactions with other biomolecules. The compound is of interest in research related to redox biology and the study of oxidative damage in cells. Additionally, it may have implications in the development of therapeutic agents targeting oxidative stress-related conditions.

Formula: C₄H₉NO₄S

InChI: InChI=1S/C4H9NO4S/c5-3(4(6)7)1-2-10(8)9/h3H,1-2,5H2,(H,6,7)(H,8,9)/t3-/m0/s1

InChI key: InChIKey=PDNJLMZEGXHSCU-VKHMYHEASA-N

SMILES: [C@H](CCS(=O)O)(C(O)=O)N

Synonyms:

• (2S)-2-amino-4-sulfinobutanoic acid
• <span class="text-smallcaps">L</span>-Homocysteine sulfinate
• <span class="text-smallcaps">L</span>-Homocysteinesulfinic acid
• Butanoic acid, 2-amino-4-sulfino-, (2S)-
• Butanoic acid, 2-amino-4-sulfino-, (S)-
• Butyric acid, 2-amino-4-sulfino-, <span class="text-smallcaps">L</span>-
• L-Homocysteinesulfinic acid
• Butyric acid, 2-amino-4-sulfino-, L-

L-Homocysteinesulfinic Acid

Controlled Product

CAS: 2686-70-6

Stability Hygroscopic
Applications L-Homocysteinesulfinic Acid has proven to be a potent and selective metabotropic glutamate receptor agonist which may be related to diseases associated with moderate hyperhomocysteinemia. Used in biosynthesis of dipthamide
References Shi, Q., et al.: J. Pharmacol. Exp. Ther., 305, 131 (2003); Zhang, Y., et al.: Nature, 465, 891 (2010);

Formula: C₄H₉NO₄S

Color and Shape: Neat

Molecular weight: 167.18

Ref: TR-H616000

L-Homocysteinesulfinic acid

CAS: 2686-70-6

L-Homocysteinesulfinic acid is an endogenous metabolite of the amino acid homocysteine. It is a reactive molecule that has been shown to cause neuronal death in vitro and in vivo. L-Homocysteinesulfinic acid binds to the NMDA receptor and inhibits its function, which may cause apoptosis. L-Homocysteinesulfinic acid also binds to the alpha2-adrenergic receptor and enhances uptake of glutamate, thereby causing neuronal death. L-Homocysteinesulfinic acid has been shown to be elevated in cancer patients, as well as those with a high risk for developing cancer. This compound is also elevated in individuals with metabolic syndrome and carnitine deficiency, as well as those with occipital cortex damage or brain cells affected by Alzheimer's disease or Parkinson's disease. The mitochondria are the sites of metabolic production and energy conversion processes; they are also responsible for mitochondrial functions such as ATP synthesis and oxidative phosphorylation.

Formula: C₄H₉NO₄S

Purity: Min. 95%

Molecular weight: 167.19 g/mol

Ref: 3D-CAA68670